1,2-Dichloroethane → HCID 69656572, Verbindung

HRID 857743Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 857743
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:25][CH2:24][CH2:23][C@H:19]3[C:20]([OH:22])=O)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl:26][C:27]1[CH:28]=[CH:29][C:30]([N:35]2[CH:39]=[N:38][CH:37]=[N:36]2)=[C:31]([CH:34]=1)[CH2:32][NH2:33].C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[Cl:26][C:27]1[CH:28]=[CH:29][C:30]([N:35]2[CH:39]=[N:38][CH:37]=[N:36]2)=[C:31]([CH:34]=1)[CH2:32][NH:33][C:20](=[O:22])[C@@H:19]1[CH2:23][CH2:24][CH2:25][N:18]1[C:16]([O:15][CH2:14][CH:12]1[C:13]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:17]

Komponenten

8

Edukt 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 688135Fmoc-Pro-OHHCID 11171817(5-Chloro-2-(1H-1,2,4-triazol-1-YL)phenyl)methanamine

Produkt 1

HCID 69656572HCID 69656572, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of [(9H-fluoren-9-ylmethoxy)carbonyl]-L-proline (3.23 g, 9.59 mmol), 1-[5-chloro-2-(1H-1,2,4-triazol-1-yl)phenyl]methanamine (Example 4, 2.00 g, 9.59 mmol, 1.0 equiv), EDC (2.76 g, 14.38 mmol, 1.5 equiv) and HOAt (652 mg, 4.79 mmol, 0.5 equiv) in DMF (5 mL) was brought to pH 6 by dropwise addition of Hünig's Base and stirred at room temperature for 18 h. The reaction was diluted with water and extracted into EtOAc three times. The combined organic layers were dried (anhydrous Na2SO4) and concentrated. The resulting oil was suspended and rigorously stirred in water to afford the title compound as white solid upon filtration. 1H NMR (400 MHz, CD3OD): δ 8.77 (m, 1 H), 8.24–8.22 (m, 1 H), 7.81–7.75 (m, 2 H), 7.66–7.62 (m, 2 H), 7.54–7.50 (m, 1 H), 7.45–7.31 (m, 5 H), 7.25–7.19 (m, 1 H), 4.43–4.36 (m, 2 H), 4.30–4.20 (m, 3 H), 4.05–4.02 (m, 1 H), 3.55–3.40 (m, 2 H), 2.28–2.18 (m, 1 H), 1.91–1.88 (m, 3 H). LCMS (M+H): 528.0.

Aufarbeitung

  1. extractionextracted into EtOAc three times
  2. dry with materialThe combined organic layers were dried (anhydrous Na2SO4)
  3. concentrationconcentrated
  4. stirringrigorously stirred in water

Quellen und Nachweise

ORD-Eintrag
ord-c3d3712c6e774bd5a2d12f9bf7d2d876
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07144899B2

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